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Improving Ibuprofen Solubility by Surfactant-Facilitated Self-Assembly Into Mixed Micelles

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Improving Ibuprofen Solubility by Surfactant-Facilitated Self-Assembly Into Mixed Micelles This is final peer-reviewed manuscript accepted for publication in Journal of Drug Delivery Science and Technology 36, 208–215, 2016, DOI: 10.1016/j.jddst.2016.10.011 Improving Ibuprofen solubility by surfactant-facilitated self-assembly into mixed micelles Katerina Stoyanovaa, Zahari Vinarov*a, Slavka Tcholakovaa aDepartment of Chemical & Pharmaceutical Engineering, Faculty of Chemistry & Pharmacy, Sofia University, 1164 Sofia, Bulgaria *Corresponding author: Assist. Prof. Zahari Vinarov Department of Chemical and Pharmaceutical Engineering Faculty of Chemistry and Pharmacy, Sofia University 1 James Bourchier Ave., 1164 Sofia Bulgaria Phone: (+359-2) 962 5310 Fax: (+359-2) 962 5643 E-mail: [email protected] Running head: Surfactant-facilitated self-assembly of Ibuprofen into mixed micelles Abstract Ibuprofen is a poorly water-soluble drug, characterized by dissolution-limited oral bioavailability. One approach to improve its water solubility and bioavailability is by solubilizing it in micellar surfactant solutions. Here we investigate the effect of the surfactant type and the mechanism of solubility enhancement of Ibuprofen in surfactant solutions. The equilibrium Ibuprofen solubility in solutions of six surfactants was determined by HPLC. The nonionic surfactant polysorbate 80 (Tween 80), and the anionic surfactants sodium dodecyl sulfate (SDS) and sodium lauryl ethoxy (3) sulfate (SLES-3EO) improve the Ibuprofen solubility by a factor of 200, as compared to the solubility in water. The highest Ibuprofen solubility is observed in SDS and SLES-3EO solutions, containing 0.6 M NaCl. The mole fraction of Ibuprofen in the micelles and the transfer energy of Ibuprofen molecules from the aqueous phase into the micelle environment were determined by thermodynamic analysis of the solubility data. The maximum Ibuprofen mole fraction in the micelles of all studied surfactants is exceptionally high (between 0.4 and 0.6). Thus we can conclude that the main mechanism of Ibuprofen solubility enhancement is a self- assembly within mixed micelles with the main surfactant. The energy of co-micellization is estimated to be around 14kT per Ibuprofen molecule. Keywords: Ibuprofen, poorly water-soluble drugs, mixed micelles, solubilization, oral bioavailability. 1 Page 2 of 19 2 1. INTRODUCTION 3 More than 40 % of the new chemical entities that emerge from modern drug discovery programs 4 are characterized by poor water solubility [1]. The slow and incomplete dissolution of such drugs in the 5 gastro-intestinal fluids limits their oral bioavailability and presents a significant problem in drug 6 development. One of the classical approaches to improve the water solubility of hydrophobic drugs, which 7 is still being used in the pharmaceutical industry, is to use appropriate surfactants [2-5]. 8 Surfactants are a large group of pharmaceutical excipients, which are used in a variety of drug 9 delivery vehicles as solubilizers, emulsifiers, foamers, wetting agents, etc. [6]. Above the critical micelle 10 concentration (CMC) the surfactant molecules form micelles [7]: molecular aggregates which have a 11 hydrophobic core and a hydrophilic surface. The hydrophobic interior of the micelles provides a suitable 12 environment for hydrophobic molecules, which leads to the solubilization phenomenon [6-8], namely, a 13 significant increase of the solubility of poorly water-soluble molecules in the micellar solutions, due to 14 their incorporation in the surfactant micelles. On the other hand, amphiphilic drugs like nortriptyline 15 hydrochloride and promazine hydrochloride can form mixed micelles with the classical surfactants [9,10] 16 which also leads to a strong enhancement of their solubility. 17 In the current article we investigate the effect of surfactants on the solubility of the non-steroidal 18 anti-inflammatory drug Ibuprofen (IBP), which is used to relieve pain, fever and inflammation. IBP is a 19 weak acid with pKa ≈ 4.4, solubility in water around 11 μg/mL, and high membrane permeability [11]. 20 Since the IBP molecule can ionize, its solubility depends strongly on the solution pH. Thus, IBP is poorly 21 soluble in the stomach, where pH ranges between 2 and 3 [12], whereas its solubility increases 22 significantly in the small intestine (pH between 4.5 and 7.5 [13]). For example, IBP solubility at pH 5 and 23 7.5 is 140 and 2300 μg/mL, respectively [14]. 24 However, the drug solubility in water per se does not provide direct information whether the drug 25 will be sufficiently soluble in the gastro-intestinal tract. The orally administered drug dose differs 26 strongly, depending on the drug type and the therapeutical application. The Biopharmaceutical 27 Classification System (BCS), introduced by Amidon et al. [15], defines the so-called “dose number” (Do), 28 which takes into account both the drug dose per given volume and the equilibrium drug solubility. Thus, 29 drugs for which Do ≤ 1 are classified as highly soluble, whereas all others have poor water solubility [16]. 30 The maximum single dose of IBP is relatively high (800 mg) and for this reason IBP’s Do is 31 always bigger than one: Do = 290 at pH = 2 (approximate conditions in the stomach) and Do = 1.4 at pH = 32 7.5 (maximum pH value in the small intestine). Thus we see that the IBP concentration in the stomach 33 fluids, after oral administration of 800 mg IBP, is 290 times higher than the equilibrium IBP solubility 34 under these conditions. As a result, IBP is characterized by poor water solubility and is classified as Class 35 ІІ drug according to BCS [17]. 36 There are different approaches for enhancing IBP delivery: controlled-release formulations [18- 37 20], lipid-based drug delivery systems [21-23], nano-particles [24,25], vesicles [26] or solubilization by 38 surfactants [27-29]. 39 Surfactants are reported to increase significantly IBP solubility [27-29] and are thus expected to 40 improve its oral bioavailability. The effect of the concentration of sodium dodecyl sulfate (SDS), dodecyl 41 octa(ethylene oxide) (C12E8) and dodecyltrimethyl-ammonium bromide (DTAB) on the IBP 42 solubilization at pH 7.4 was studied by Stephenson et al. [27]. These authors found that the aqueous Page 3 of 19 43 solubility of IBP increases linearly with surfactant concentration for these surfactants. The highest 44 solubilization was observed upon the addition of DTAB, followed by C12E8 and SDS. A molecular- 45 thermodynamic modeling approach was developed to predict theoretically the solubilization behavior of 46 these systems. The obtained theoretical results on the IBP solubility in SDS and C12E8 solutions were in a 47 good agreement with the experimental data. 48 Kokot & Zmidzinska [28] studied the IBP solubilization in unbuffered SDS, Brij 35 and Tween 60 49 surfactant solutions. They reported a significant increase of IBP solubility and no specific effect of the 50 surfactant type. 51 Park et al. studied the saturation solubility of IBP [29] and showed that at pH = 1.2, highest 52 solubility is obtained with solutions of cetyltrimethylammonium bromide (CTAB), compared to much 53 lower solubility for Tween 80 and SDS. The better IBP solubilization in CTAB, compared to SDS 54 solutions, was explained by attractive electrostatic interactions, without accounting for the longer 55 hydrophobic chain length of CTAB. The authors reported also a higher dissolution rate of IBP tablets in 56 surfactant solutions, relative to pure water. 57 None of the above studies has provided mechanistic explanation for the observed very strong 58 effects of surfactants on IBP solubility. Therefore, the aim of the current article is to clarify (1) the 59 mechanism of IBP solubility enhancement in surfactant solutions and (2) the effect of the surfactant type. 60 To achieve this aim we determined experimentally the effect of four nonionic (Tween 20, 40, 60 and 80) 61 and two anionic (SDS and SLES-3EO) surfactants on the IBP solubility. The mechanism of improved IBP 62 solubility and the strength of the drug-surfactant interactions are analyzed using a thermodynamic 63 treatment of the solubility data. 64 65 2. MATERIALS AND METHODS 66 2.1. Materials. 67 2.1.1. Drug and surfactants. 68 We used IBP (see Figure 1), product of Sigma Aldrich (MW = 206.29 g/mol, purity 99 %, cat. no. 69 I4883). To increase the drug solubility, we used several nonionic and anionic surfactants. Table 1 provides 70 information about all studied surfactants: type, trade name/abbreviation used in the text, purity, molecular 71 weight, chemical formula, producer, and critical micelle concentration (CMC). The molecular structures 72 of the studied surfactants are presented in Figure 2. 73 74 75 76 77 Figure 1. Molecular structure of IBP. 78 Page 4 of 19 79 Table 1. Studied surfactants. 80 Type of Trade name/ Purity, Molecular 81 Producer CMC, mM surfactant abbreviation wt% mass, g/mol 82 Tween 20 100 1228 Sigma 0.08 [30] 83 Tween 40 100 1277 Sigma 0.027 [31] Nonionic 84 Tween 60 100 1309 Sigma 0.017 [31] 85 Tween 80 100 1310 Sigma 0.023 [31] 86 SDS 99 288 Acros 8.0 [32] Anionic 87 SLES 3 EO 70 420 Stepan Co. 0.5 [33] 88 89 90 91 92 93 94 95 96 97 98 99 100 101 Figure 2. Molecular structures of the studied surfactants. 102 103 Page 5 of 19 104 2.1.2. Buffer solutions, solvents for HPLC and water. 105 To prepare the buffer solutions we used H3PO4 (85 %, Merck, cat. no. 100563), NaH2PO4 (99 %, 106 Fluka Analytical, cat. no. 71504), Na2HPO4.7H2O (99 %, Riedel de Haën, cat. no. 30413), CH3COOH 107 (100 %, Merck, cat. no. 100056) and CH3COONa.3H2O (99 %, Merck, cat. no. 106267). 108 The mobile phase solvents for HPLC analysis include acetonitrile (HPLC grade, 99 %) and 20 mM 109 aqueous solutions of CH3COOH and CH3COONa. All aqueous solutions and buffers were prepared using 110 deionized water from water-purification system Elix 3 (Millipore, USA).
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